This paper is a narrative review examining the high prevalence of care leaver early parenting in the context of (i) key transitions from care studies taken from the last few decades, (ii) a structured review using Scopus of studies from 2015–2020 focussed specifically on young people transitioning from care and early parenting and (iii) Boss’s (2010) Ambiguous Loss theory. Young care leavers’ challenges, in general, put them at higher risk of protective interventions with their children and may contribute to the growing numbers of children being placed in increasingly over-stretched out-of-home care systems. Questions of surveillance bias for service-connected young people are examined in light of recent large-scale studies using administrative data sets. Serious oversights in responding to young people’s experiences of trauma and exploitation are identified. The relevance of sexual health programs for young people actively seeking pregnancies is discussed with emerging evidence that disengagement from schooling may have more of a role in explaining early pregnancy and parenting than previously thought. The authors test the relevance of Ambiguous Loss theory in understanding how removal from families of origin and placement experiences may affect young people and lead to ‘wanted’ pregnancies.